DE69610477T2 - 5H- THIAZOLO(3,2-a)PYRIMIDIN-5-ON-DERIVATE - Google Patents
5H- THIAZOLO(3,2-a)PYRIMIDIN-5-ON-DERIVATEInfo
- Publication number
- DE69610477T2 DE69610477T2 DE69610477T DE69610477T DE69610477T2 DE 69610477 T2 DE69610477 T2 DE 69610477T2 DE 69610477 T DE69610477 T DE 69610477T DE 69610477 T DE69610477 T DE 69610477T DE 69610477 T2 DE69610477 T2 DE 69610477T2
- Authority
- DE
- Germany
- Prior art keywords
- thiazolo
- pyrimidin
- derivatives
- pct
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- UEZROEGYRDHMRV-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical class O=C1C=CN=C2SC=CN12 UEZROEGYRDHMRV-UHFFFAOYSA-N 0.000 title claims abstract description 7
- -1 methylendioxy Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 208000019901 Anxiety disease Diseases 0.000 claims abstract 2
- 201000000980 schizophrenia Diseases 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 8
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 7
- 108091005479 5-HT2 receptors Proteins 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 101150049660 DRD2 gene Proteins 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000009194 climbing Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
- UOXKUQKPZHYGEJ-UHFFFAOYSA-N 6-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-3-(4-fluorophenyl)-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound N12C(=O)C(CCN3CCC(CC3)C=3C4=CC=C(F)C=C4ON=3)=C(C)N=C2SC=C1C1=CC=C(F)C=C1 UOXKUQKPZHYGEJ-UHFFFAOYSA-N 0.000 description 4
- 206010028347 Muscle twitching Diseases 0.000 description 4
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
- 229960004046 apomorphine Drugs 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000009870 specific binding Effects 0.000 description 4
- HIEQQWXPKKNASS-UHFFFAOYSA-N 6-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-3-(4-methoxyphenyl)-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1=CC(OC)=CC=C1C(N1C2=O)=CSC1=NC(C)=C2CCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 HIEQQWXPKKNASS-UHFFFAOYSA-N 0.000 description 3
- 208000009132 Catalepsy Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229960003878 haloperidol Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- UJOCFQKQSHJIHT-UHFFFAOYSA-N 6-(2-chloroethyl)-7-methyl-3-(4-methylphenyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1=CC(C)=CC=C1C1=CSC2=NC(C)=C(CCCl)C(=O)N12 UJOCFQKQSHJIHT-UHFFFAOYSA-N 0.000 description 2
- WRTJOXGDIGMSMH-UHFFFAOYSA-N 6-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-7-methyl-3-(4-methylphenyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1=CC(C)=CC=C1C(N1C2=O)=CSC1=NC(C)=C2CCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 WRTJOXGDIGMSMH-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000005567 liquid scintillation counting Methods 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229950001675 spiperone Drugs 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- BGMZUEKZENQUJY-UHFFFAOYSA-N 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1I BGMZUEKZENQUJY-UHFFFAOYSA-N 0.000 description 1
- ARLHWYFAPHJCJT-UHFFFAOYSA-N 4-(4-methylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(C)=CC=C1C1=CSC(N)=N1 ARLHWYFAPHJCJT-UHFFFAOYSA-N 0.000 description 1
- TVQJFCNJXMSJAC-UHFFFAOYSA-N 6-(2-chloroethyl)-3-(4-methoxyphenyl)-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1=CC(OC)=CC=C1C1=CSC2=NC(C)=C(CCCl)C(=O)N12 TVQJFCNJXMSJAC-UHFFFAOYSA-N 0.000 description 1
- MRMGJMGHPJZSAE-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C1CCNCC1 MRMGJMGHPJZSAE-UHFFFAOYSA-N 0.000 description 1
- CWPSRUREOSBKBQ-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1,2-benzoxazole;hydrochloride Chemical compound Cl.N=1OC2=CC(F)=CC=C2C=1C1CCNCC1 CWPSRUREOSBKBQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010876 biochemical test Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229960005417 ketanserin Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229960003955 mianserin Drugs 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES09501029A ES2097093B1 (es) | 1995-05-26 | 1995-05-26 | Nuevos compuestos derivados de 5h-tiazolo (3,2-a) pirimidin-5-ona. |
| PCT/EP1996/002254 WO1996037498A1 (en) | 1995-05-26 | 1996-05-24 | 5H-THIAZOLO[3,2-a]PYRIMIDIN-5-ONE DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69610477D1 DE69610477D1 (de) | 2000-11-02 |
| DE69610477T2 true DE69610477T2 (de) | 2001-05-10 |
Family
ID=8290506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69610477T Expired - Fee Related DE69610477T2 (de) | 1995-05-26 | 1996-05-24 | 5H- THIAZOLO(3,2-a)PYRIMIDIN-5-ON-DERIVATE |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5798361A (no) |
| EP (1) | EP0773947B1 (no) |
| JP (1) | JPH10503782A (no) |
| AT (1) | ATE196633T1 (no) |
| AU (1) | AU698455B2 (no) |
| CA (1) | CA2195578A1 (no) |
| DE (1) | DE69610477T2 (no) |
| DK (1) | DK0773947T3 (no) |
| ES (1) | ES2097093B1 (no) |
| IL (1) | IL118280A (no) |
| MX (1) | MX9601953A (no) |
| NO (1) | NO308304B1 (no) |
| NZ (1) | NZ308533A (no) |
| PT (1) | PT773947E (no) |
| TW (1) | TW430666B (no) |
| WO (1) | WO1996037498A1 (no) |
| ZA (1) | ZA964091B (no) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443451A (en) * | 1981-07-15 | 1984-04-17 | Janssen Pharmaceutica N.V. | Bicyclic pyrimidin-5-one derivatives |
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| KR100251892B1 (ko) * | 1992-07-13 | 2000-09-01 | 디르크 반테 | 신규한 4-(3-벤조푸라닐)피페리디닐 및 4-(3-벤조티에닐)피페리디닐 유도체 및 이들을 함유하는 약제학적 조성물 |
-
1995
- 1995-05-26 ES ES09501029A patent/ES2097093B1/es not_active Expired - Lifetime
-
1996
- 1996-05-14 TW TW085105655A patent/TW430666B/zh not_active IP Right Cessation
- 1996-05-15 IL IL11828096A patent/IL118280A/xx not_active IP Right Cessation
- 1996-05-22 ZA ZA964091A patent/ZA964091B/xx unknown
- 1996-05-23 MX MX9601953A patent/MX9601953A/es not_active IP Right Cessation
- 1996-05-24 EP EP96919807A patent/EP0773947B1/en not_active Expired - Lifetime
- 1996-05-24 US US08/765,935 patent/US5798361A/en not_active Expired - Fee Related
- 1996-05-24 NZ NZ308533A patent/NZ308533A/en unknown
- 1996-05-24 PT PT96919807T patent/PT773947E/pt unknown
- 1996-05-24 AU AU58203/96A patent/AU698455B2/en not_active Ceased
- 1996-05-24 JP JP8535401A patent/JPH10503782A/ja active Pending
- 1996-05-24 CA CA002195578A patent/CA2195578A1/en not_active Abandoned
- 1996-05-24 WO PCT/EP1996/002254 patent/WO1996037498A1/en not_active Application Discontinuation
- 1996-05-24 DK DK96919807T patent/DK0773947T3/da active
- 1996-05-24 DE DE69610477T patent/DE69610477T2/de not_active Expired - Fee Related
- 1996-05-24 AT AT96919807T patent/ATE196633T1/de not_active IP Right Cessation
-
1997
- 1997-01-24 NO NO970327A patent/NO308304B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT773947E (pt) | 2001-01-31 |
| AU5820396A (en) | 1996-12-11 |
| NZ308533A (en) | 1997-11-24 |
| NO970327D0 (no) | 1997-01-24 |
| TW430666B (en) | 2001-04-21 |
| ES2097093B1 (es) | 1998-01-16 |
| EP0773947B1 (en) | 2000-09-27 |
| MX9601953A (es) | 1997-08-30 |
| NO970327L (no) | 1997-01-24 |
| ES2097093A1 (es) | 1997-03-16 |
| US5798361A (en) | 1998-08-25 |
| IL118280A0 (en) | 1996-09-12 |
| CA2195578A1 (en) | 1996-11-28 |
| ATE196633T1 (de) | 2000-10-15 |
| DK0773947T3 (da) | 2000-10-16 |
| JPH10503782A (ja) | 1998-04-07 |
| AU698455B2 (en) | 1998-10-29 |
| WO1996037498A1 (en) | 1996-11-28 |
| DE69610477D1 (de) | 2000-11-02 |
| IL118280A (en) | 1999-10-28 |
| EP0773947A1 (en) | 1997-05-21 |
| NO308304B1 (no) | 2000-08-28 |
| ZA964091B (en) | 1997-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69631370T2 (de) | Benzylpiperidine und -piperazine als muscarinantagonisten | |
| DE69333597T2 (de) | Benzisothiazol-Piperazinylderivat und seine Verwendung als Neuroleptikum | |
| DE69108461T2 (de) | 1-Indolylalkyl-4-(alkoxy-pyrimidinyl)piperazine. | |
| DE69613240T2 (de) | N-aminoalkylfluorencarboxamide, neue klasse von dopaminerezeptor subtype spezifische liganden | |
| DE3781173T2 (de) | N-heterozyklische-4-piperidinamine enthaltende anti-histaminische zusammensetzungen. | |
| CH660484A5 (de) | In 1-stellung durch einen heterocyclischen rest substituierte 4-((2,5-pyrrolidindion-1-yl)alkyl)piperazin-verbindungen. | |
| DE69815700T2 (de) | Tetrahydro gamma-carboline | |
| DE3877470T2 (de) | Oxazole und thiazole zur behandlung seniler demenz. | |
| DE69733427T2 (de) | Tetrahydrobezindol derivate | |
| DE69214588T2 (de) | Methanoanthracene als Dopaminantagonisten | |
| DE69427517T2 (de) | Tetracyclische kondensierte heterocyclische Verbindungen zur Behandlung von seniler Demenz | |
| DE69722281T2 (de) | 3-Aza-piperidon- (Tetrahydropyrimidin-2-on) und 3-Oxa-piperidon (1,3-Oxazin-2-on) Derivate, deren Herstellung und deren Verwendung als Tachykinin/Neurokinin Antagonisten | |
| DE60123643T2 (de) | Benzimidazolonderivate mit affinität zu serotonin- und dopaminrezeptoren | |
| DE69824872T2 (de) | 1,2,3,4-tetrahydro-benzofuro[3,2-c]pyridin derivate | |
| DE69611783T2 (de) | Benzisoxazol- und indazol- derivate als antipsychotika | |
| DE602005006018T2 (de) | Arylpiperazinderivate und deren verwendung als für den dopamin-d3-rezeptor selektive liganden | |
| DE69211892T2 (de) | 1-(Pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-Indole, Zwischenprodukte und ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE69519047T2 (de) | Benzodioxan Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen | |
| DE69720715T2 (de) | Hexahydro-pyrido (4,3-b)indolderivate als antipsychotische arzneimittel | |
| DE69623610T2 (de) | Neue heterozyklische chemie | |
| DE69814563T2 (de) | Pyrrolo-(3,2-b)pyridine und ihre Verwendung als 5-HT1F Agonisten | |
| DE69225625T2 (de) | Carbaminsäurederivate und Verfahren zu ihrer Herstellung | |
| DE3785393T2 (de) | 4-(aroylamino)piperidinbutanamide derivate. | |
| DE69610477T2 (de) | 5H- THIAZOLO(3,2-a)PYRIMIDIN-5-ON-DERIVATE | |
| EP0168812A1 (de) | 4-Amino-2-phenylchinoline, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |